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18.6.5.1.2.4.1 Variation 1: Hydrolysis of Thiocyanates

DOI: 10.1055/sos-SD-018-00578

Rossi, L.Science of Synthesis, (200518613.

The reaction of thiocyanates with concentrated sulfuric acid and ice water gives the corresponding thiocarbamates 313 (Scheme 220). The reaction proceeds smoothly with aromatic[‌523‌] and primary aliphatic thiocyanates,[‌524‌,‌525‌] but secondary thiocyanates are less reactive. tert-Butyl thiocyanate is not reactive at all. In addition, the reaction is unsatisfactory in the case of several 2-substituted phenyl thiocyanates which are sensitive to concentrated sulfuric acid.

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